Acetaldehyde → HCID 57457555, compound

HRID 2386949Notes

Reaction equation

HRID 2386949 reaction equation
C([N-]C(C)C)(C)C.[Li+].[C:9]1([C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][O:11]1)=[O:10].[CH:19](=[O:21])[CH3:20]>O1CCCC1>[OH:21][CH:19]([CH:12]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=2[C:9](=[O:10])[O:11]1)[CH3:20]

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 6885PhthalideHCID 2724682Lithium diisopropylamide

Product 1

HCID 57457555HCID 57457555, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A dry tetrahydrofuran solution (100 mL) of lithium diisopropyl amide (26.9 mmol) was cooled to −78 degree in a current of nitrogen, and a tetrahydrofuran solution (100 mL) of phthalide (3.0 g, 22.4 mmol) was dripped in. After stirring at −78° C. for 30 minutes, acetaldehyde (1.19 g, 26.9 mmol) was slowly added and stirred at −50° C. for 4 hours. After the temperature had risen to room temperature, distilled water was added and the mixture extracted with ethyl acetate. The organic phase was washed with distilled water and saturated brine, and dried with anhydrous sodium sulfate. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/6), and the target compound (1.96 g, 49%) was obtained as a yellow oily residue.

Workup

  1. stirringstirred at −50° C. for 4 hours
  2. customhad risen to room temperature
  3. distillationdistilled water
  4. additionwas added
  5. extractionthe mixture extracted with ethyl acetate
  6. washThe organic phase was washed with distilled water and saturated brine
  7. dry with materialdried with anhydrous sodium sulfate
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/6)

Sources & evidence

ORD record
ord-6c88743586254ec4b1a29f464ee22971
Source dataset
uspto-grants-2012_09
Patent number
US08268842B2

Reaction notes

Loading…